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Potassium Hydroxide → 2-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid

HRID 1062250
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인쇄 미리보기

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HRID 1062250 반응식
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[CH2:18][C:19](=[O:35])[NH:20][C:21]4[CH:27]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=5)[CH:25]=[CH:24][C:22]=4[N:23]=3)[CH:12]=2)[S:9][CH:10]=1)=[O:5])C.[OH-].[K+]>CO.CS(C)=O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:26]2[CH:25]=[CH:24][C:22]3[N:23]=[C:17]([C:13]4[CH:12]=[C:11]([C:8]5[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=5)[CH:16]=[CH:15][CH:14]=4)[CH2:18][C:19](=[O:35])[NH:20][C:21]=3[CH:27]=2)=[CH:29][CH:30]=1
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참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 695928182-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester

생성물 1

HCID 222249612-{3-[7-(4-Fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid수율 54.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 887
Methanol
용매

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온도
23 °C

실험 절차

To a solution of 2-{3-[7-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-yl]-phenyl}-thiazole-4-carboxylic acid ethyl ester (Example 153) (49 mg, 0.1 mmol) in a mixture of MeOH (1 mL) and DMSO (1.5 mL) was added 2N KOH (1 mL, 2 mmol). The mixture was stirred at 23° C. for 0.5 h and then partitioned between ethyl acetate and H2O. The pH of the aqueous phase was set to 3 by the addition of 3N HCl and then stirred in the ice-bath for 0.5 h. The precipitate was collected by filtration, triturated with EtOH/Et2O (1/1) and dried, to give the title compound as light yellow solid (25 mg).

후처리

  1. custompartitioned between ethyl acetate and H2O
  2. additionThe pH of the aqueous phase was set to 3 by the addition of 3N HCl
  3. stirringstirred in the ice-bath for 0.5 h
  4. filtrationThe precipitate was collected by filtration
  5. customtriturated with EtOH/Et2O (1/1)
  6. customdried

출처 및 근거

ORD 기록
ord-e1064f2fe1994d939386f1d14d0af204
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06960578B2

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